Old San Juan Orientation Walk, San Juan (Self Guided)

San Juan, the capital of Puerto Rico, is a lovely historic city with a wealth of colorful Spanish colonial architecture. The most notable landmarks include 16th-century El Morro and La Fortaleza fortresses, rising above the ocean, and the Paseo de la Princesa bayside promenade. To explore San Juan's most prominent sights, follow this orientation walk.
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Old San Juan Orientation Walk Map

Guide Name: Old San Juan Orientation Walk
Guide Location: Puerto Rico » San Juan (See other walking tours in San Juan)
Guide Type: Self-guided Walking Tour (Sightseeing)
# of Attractions: 15
Tour Duration: 3 hour(s)
Travel Distance: 4.9 km
Author: leticia
Plaza de Armas (Arms Square)

1) Plaza de Armas (Arms Square) (must see)

Plaza de Armas is located on San José Street in front of the Spanish colonial style building Casa Alcaldía. This historic square contains four beautiful statues symbolizing the seasons and a wonderful fountain. Built over 100 years ago as the main city square, Plaza de Armas was an important social meeting place for generations and is now a popular tourist attraction.
Calle de la Fortaleza

2) Calle de la Fortaleza

La Calle de la Fortaleza is a street artery in the historic quarter of Old San Juan , Puerto Rico . At the beginning of this street is the call: " Fortress" or "Palace of Santa Catalina " and ends at Plaza Colón . It is a narrow street in which there are from government offices, hotels, perfumeries, craft shops, jewelry stores and restaurants. Its continuation to the east is the Avenue Juan Ponce de León .

It is well-known, like the rest of the streets of the old city, to have transformed into an important tourist center, due to its historical and cultural importance for the city. In holidays and cultural activities it is pedestrianized in all or almost all its extension.
Sight description based on wikipedia
Fort San Cristóbal

3) Fort San Cristóbal (must see)

Castillo de San Cristóbal was built by Spain as protection against land attacks on San Juan. It is listed as a San Juan National Historic Site. Castillo de San Cristóbal is the largest fortification built by the Spanish in the New World. When it was finished in 1783, it covered about 27 acres of land and basically wrapped around the city. Entry to the city was sealed by San Cristóbal's double gates. After a period of relative peace, about a third of it was demolished in 1897 to help ease the flow of traffic in and out of the city. Nowadays guided tours by park personnel are available. You can visit the extensive tunnel system connecting the various sections of the fort or see the historic weapons firing drill, and the artillery observation post built by the U.S. Army during World War II. An exhibition of military clothing is also available, and also real 200-pound mortar shells.
Sight description based on wikipedia
La Princesa Fountain

4) La Princesa Fountain

Located in Paseo de la Princesa is the Raíces (Roots) Fountain. This beautiful bronze fountain reflecting Puerto Rico’s rich cultural heritage and diversity is a popular tourist attraction.
Capilla Del Santo Cristo de la Salud (Cristo Chapel)

5) Capilla Del Santo Cristo de la Salud (Cristo Chapel) (must see)

Capilla Del Santo Cristo de la Salud is small chapel dating back to 1753. Over the centuries this beautiful chapel was a lovely place of worship to thousands of people. As a legend tells, this historical structure was built to commemorate a miracle.
La Fortaleza

6) La Fortaleza (must see)

La Fortaleza, or the Fortress, is the current official residence of the Governor of Puerto Rico. It was built between 1533 and 1540 to defend the harbor of San Juan. It is the oldest executive mansion in the New World. It was listed by UNESCO in 1983 as a World Heritage Site. During the 1640 reconstruction, the chapel of Santa Catalina, then located outside the walls, was demolished and was integrated into it, which gave rise to another name for which it is known, Palacio de Santa Catalina.
La Fortaleza was the first defensive fortification built for the city of San Juan, and the first of a series of military structures built to protect the city which included the Fort San Felipe del Morro and the Fort San Cristóbal. The fortress underwent a massive reconstruction in 1846 to change its military appearance into a palatial facade. La Fortaleza has been the residence of more than 170 governors of Puerto Rico and has hosted various dignitaries, including President John F. Kennedy and his wife Jacqueline Kennedy who stayed in La Fortaleza in 1961. The construction was authorized by Charles V, Holy Roman Emperor as a defense against attacks from Carib Indians and the European powers of the time. At present, the complex consists of a few attached buildings with formal living quarters in the second floor, and private quarters in the third. It overlooks the high city walls that front the bay, and within the north perimeter of the house are sheltered gardens and a swimming pool.
Sight description based on wikipedia
Puerta de San Juan (San Juan Gate)

7) Puerta de San Juan (San Juan Gate) (must see)

Puerta de San Juan is a famous city gate built in the late 1700s. This 40 feet high red gate, built to protect the city from invaders, is one of six impressive wooden doors which were closed at sundown for centuries. If you turn right after passing through the gate, you will find the way to Fort del Morro.
La Muralla (City Wall)

8) La Muralla (City Wall) (must see)

La Muralla, or the City Wall, is one of the most precious historic landmarks and a popular tourist attraction in Puerto Rico. Its construction began in 1539 and was finished in 1782. Built to protect the city from invaders, it is made of sandstone blocks as much as 20 feet thick. The city walls, of which only the north part can be appreciated, as the east part is practically destroyed. It is currently being restored. They originally had five doors and formed a triangle with the castle in its superior vertex. The two sides of the triangle are formed by the rivers Arevalillo and Adaja. The base of the triangle was protected by a double wall and a pit.
Cathedral of San Juan Bautista

9) Cathedral of San Juan Bautista (must see)

The Cathedral of San Juan Bautista is the Roman Catholic cathedral of the Archdiocese of San Juan de Puerto Rico. The cathedral is one of the oldest buildings in San Juan, located in Old San Juan, and is the second oldest cathedral in the Americas. The Cathedral of Santa María la Menor in Santo Domingo in the Dominican Republic, is the oldest. The original cathedral in what was the city of Puerto Rico (changed to San Juan after the Spanish-American War) was constructed from wood in 1521. It was destroyed by a hurricane and the current structure constructed in 1540, being reshaped in later centuries, the last time being in 1917.

The first school in Puerto Rico (and the oldest school in the United States after Puerto Rico became a territory of the United States) was the Escuela de gramática (Grammar School). The school was established by Bishop Alonso Manso in 1513, in the area where the cathedral would later be constructed. The school was free of charge and the courses taught were Latin language, literature, history, science, art, philosophy and theology.

The cathedral contains the tomb of the Spanish explorer and settlement founder Juan Ponce de León. It also has a shrine to the Blessed Carlos Manuel Rodríguez Santiago, the first Puerto Rican, the first Caribbean-born layperson and the first layperson in the history of the United States to be beatified.
Sight description based on wikipedia
Eugenio Maria De Hostos

10) Eugenio Maria De Hostos

This monument is located at Parque de Benefecia, near the prominent Cuartel de Ballajá. It is dedicated to Eugenio Maria de Hostos, a famous Puerto Rican intellectual, teacher, lawyer, philosopher and advocate. The sculpture was created by the renowned sculptor José Buscaglia Guillermety. The monument features Eugenio Maria de Hostos with children dancing on him.
Plaza de Beneficencia

11) Plaza de Beneficencia

Plaza de Beneficencia, located near Escuela de Artes Plasticas, is on the list of San Juan Historical Sites. This former place of battle is now a green area with an amazing view of Castillo San Filipe del Morro.
El Castillo San Felipe del Morro

12) El Castillo San Felipe del Morro (must see)

Fort San Felipe del Morro, or El Castillo San Felipe del Morro in Spanish, is a 16th century citadel on the northwestern-most point of San Juan. Named in honor of King Philip II of Spain, the fort was designed to guard the entrance to San Juan bay and defend the city from seaborne invaders. In 1983, it was declared a World Heritage Site by the United Nations. Over two million visitors a year explore the windswept ramparts and passageways, making the fort one of Puerto Rico's main attractions. The construction of the Castillo San Felipe del Morro and its surrounding walls began in 1539 when King Charles V of Spain authorized its construction. Many complex additional new structures were added to El Morro over the next 400 years to keep up with the new military technologies. For example, El Morro's outer walls, which were originally constructed six meters thick, were augmented to 18 feet (5.5 m) thickness by the end of the 18th century. Moreover, in 1680, Governor Enrique Enríquez de Sotomayor began the construction of the walls surrounding the city of San Juan, which took 48 years to build.
Sight description based on wikipedia
Santa María Magdalena de Pazzis Cemetery

13) Santa María Magdalena de Pazzis Cemetery (must see)

Santa María Magdalena de Pazzis Cemetery is a colonial-era cemetery located in Old San Juan, Puerto Rico. It is the final resting place of many of Puerto Rico's most prominent natives and residents. Construction began in 1863 under the auspices of Ignacio Mascaro. The cemetery is located outside the walls of Fort San Felipe del Morro fortress, one of the island's most famous landmarks. It was named in honor of Saint Maria Magdalena de Pazzi. The location of the cemetery is central to the Puerto Rican belief in the separation of death and life. The colonial Spanish government at the time the construction of the cemetery commenced, viewed death with fear because it was a mystery. Therefore, they decided to build the cemetery to overlook the Atlantic Ocean to symbolize the spirit's journey to cross over to the afterlife.
Museo de las Américas (Cuartel de Ballajá)

14) Museo de las Américas (Cuartel de Ballajá) (must see)

Museo de las Américas is located in the old Cuartel de Ballajá (Spanish military barracks). Dedicated to American culture, the museum displays changing exhibitions of paintings, carved figures, beautiful sculptures and other works by artisans from North, South and Central America.

Operation hours: Tuesday - Saturday: 9 am – 12 pm & 1 pm – 4 pm; Sunday: 12 pm - 5 pm
Plaza del Quinto Centenario (Quincentennial Square)

15) Plaza del Quinto Centenario (Quincentennial Square) (must see)

Plaza del Quinto Centenario is located on the corner of Recinto Sur and San Justo, between Cuartel de Ballajá and Iglesia San José. This plaza was built to commemorate the 500th anniversary of America’s discovery. In its center you will find Tótem Telúrico, an impressive modern sculpture.

Walking Tours in San Juan, Puerto Rico

Create Your Own Walk in San Juan

Create Your Own Walk in San Juan

Creating your own self-guided walk in San Juan is easy and fun. Choose the city attractions that you want to see and a walk route map will be created just for you. You can even set your hotel as the start point of the walk.
San Juan Historic Buildings Self-Guided Tour

San Juan Historic Buildings Self-Guided Tour

San Juan proudly features the country’s oldest quarters and historic buildings. In addition to containing the oldest occupied residence in the Western Hemisphere, visitors can also admire the old City Hall, the Cristo Chapel, Convento de los Dominicos, historic El Arsenal and many other fascinating attractions. Take the following tour to see the most popular and famous historic buildings in San...  view more

Tour Duration: 2 hour(s)
Travel Distance: 2.5 km
East San Juan Walking Tour

East San Juan Walking Tour

East San Juan contains many great attractions, including San Gerónimo Fort, Parque Luis Muñoz Rivera, beautiful statues and the best art galleries and museums. Take the following tour to discover the most interesting places in San Juan's east end!

Tour Duration: 2 hour(s)
Travel Distance: 4.8 km
Souvenir Shopping

Souvenir Shopping

It would be a pity to leave San Juan without having explored its specialty shops and bringing home something truly original. We've compiled a list of gifts and souvenirs, which are unique to San Juan, that a visitor might like to purchase to reflect their visit.

Tour Duration: 2 hour(s)
Travel Distance: 1.5 km
San Juan Art Museums And Galleries Walking Tour

San Juan Art Museums And Galleries Walking Tour

San Juan is a great place to learn more about American, Caribbean, Latin American and Puerto Rican art. It has a vast range of interesting museums and excellent galleries, featuring fine works by talented international and local artists. Check out San Juan’s most popular and outstanding art museums and galleries in this walking tour!

Tour Duration: 2 hour(s)
Travel Distance: 2.5 km
East Old San Juan Walking Tour

East Old San Juan Walking Tour

East Old San Juan is a popular tourist area that is home to several interesting historical sites, including Castillo de San Cristóbal, El Capitolio, Casa De España and Monumento de la Recordación Take the following tour to discover the fascinating attractions located in Old San Juan’s east end!

Tour Duration: 1 hour(s)
Travel Distance: 1.5 km
Old San Juan Squares Self-Guided Tour

Old San Juan Squares Self-Guided Tour

Old San Juan is packed with historical places, among which are the city’s old squares. Many of them house beautiful fountains, prominent monuments and wonderful sculptures which depict the rich history of this amazing city. Check out San Juan’s most popular historical squares in the next self-guided tour!

Tour Duration: 1 hour(s)
Travel Distance: 2.1 km

Useful Travel Guides for Planning Your Trip

15 Distinctively Puerto Rican Goods to Bring Home from San Juan

15 Distinctively Puerto Rican Goods to Bring Home from San Juan

The uniqueness of Puerto Rico is partially associated with its political status - part of the United States yet with a Latin twist. Other than their widely-acknowledged musical talents, e.g. Carlos Santana and Ricky Martin, Puerto Rico is just as rich in many other good things. When you're in...

Tips for Exploring City on Foot at Your Own Pace

Whether you are in San Juan for a quick stopover or have a few days to see the city in more detail, exploring it on foot, at your own pace, is definitely the way to go. Here are some tips for you to save money, see the best San Juan has to offer, take good care of your feet while walking, and keep your mobile device – your ultimate "work horse" on this trip - well fed and safe.

Taking Care of Your Feet

To ensure ultimate satisfaction from a day of walking around the city as big as San Juan, it is imperative to take good care of your feet so as to avoid unpleasant things like blisters, cold or overheated soles, itchy, irritated or otherwise damaged (cracked) skin, etc. Luckily, these days there is no shortage of remedies to address (and, ideally, to prevent) these and other potential problems with feet. Among them: Compression Socks, Rechargeable Battery-Powered Thermo Socks for Cold Weather, Foot Repair Cream, Deodorant Powder, Shoes UV Sterilizer, and many more that you may wish to find a place in your travel kit for.

Travel Gadgets for Your Mobile Device

Your mobile phone or tablet will be your work horse on a self-guided walk. They offer tour map, guide you from one attraction to another, and provide informative background for the sights you wish to visit. Therefore it is absolutely essential to plan against unexpected power outages in the wrong place at the wrong time, much as to ensure the safety of your device.

For these and other contingencies, here's the list of useful appliances: Portable Charger/External Battery Pack, Worldwide Travel Charger Adapter, Power Converter for International Travel Adapter, and Mobile Device Leash.